# Pushing SSH a bit further ## What is SSH ### Origins SSH is *the* current standard for remote logins but you might want to read up a bit on what was used before SSH existed. [This](https://www.jeffgeerling.com/blog/brief-history-ssh-and-remote-access) is a pretty good blog post on the history of SSH. You should never use the following the following programs anymore but it's good to be aware of their historic existance. * rlogin * rsh * rcp * telnet (still has some legitimate usage such as with munin) The main advantage of SSH is it's encryption. It works similarly to SSL which you use all the time to do most of your web browsing. When using encryption it becomes **very** hard to sniff the data traveling between the client and the server. There are two versions of SSH, version 1 and version 2, and you should only use version 2 as the former is not considered [secure]() anymore. The recommended encryption used by most SSH servers is [AES](https://en.wikipedia.org/wiki/Advanced_Encryption_Standard). If you're interested in understanding the mathematics behind AES, [this](https://www.youtube.com/channel/UC1usFRN4LCMcfIV7UjHNuQg) class is exceptionally good but not for the faint of heart. It's not mandatory to fully understand the math behind encryption to use it though. The main takeaway would be the number of **bit's used** where **higher** is **better**. By default ssh uses a very secure cipher but you can specify which one you want with the `-c` flag to `ssh`. Do keep in mind that the server needs to support the cipher you're requesting. ## SSH keys SSH encryption and SSH keys are not the same thing. **Keys** are used for **authentication** with a server. Once the client is authenticated and granted access to the server, the encryption is set to **encrypt** the **traffic** from client to server and visa versa. SSH keys are [asymmetric](https://en.wikipedia.org/wiki/Public-key_cryptography) key pairs where you have two simple text files. One with the **private** part, which is used for **decrypting**, and one **public** part which is used for **encrypting**. Both parts together form one **key pair**. If you're interested in the maths behind key pairs, have a look at this 15min [video](https://www.youtube.com/watch?v=4zahvcJ9glg&t=1s), it's a lot easier than you expect! ![key pairs](./assets/key_encryption.png) ### Generating keys SSH comes with `ssh-keygen` to generate keys. Keys are by default stored in `~/.ssh/` and named `id_rsa` for the **private** part, and `id_rsa.pud` for the **public** part. **Important**, each generated key is **unique** so if you overwrite a key you made previously that old key is **gone!**. There is **no way** to recover that old key anymore, gone is gone. I highly advise you to keep backup's of your important keys, preferably in multiple locations. GNOME [Seahorse](https://wiki.gnome.org/Apps/Seahorse/) or [keepass2](https://keepass.info/) are good password managers you can use to store both passwords and key pairs. An ssh key can be generated by running the `ssh-keygen` command. You'll be prompted with a dialog that will ask to name and where to save the key pair, plus whether you want a password for that key or not. For automated logins you should not set a password as it would defeat the purpose but you **must** realise that everyone that has access to the **private** key will be able to log in to each server the key is deployed to. Keeping this file safe becomes very important. **Remember the bandit SSH key level?** ``` ➜ ~ git:(master) ✗ ssh-keygen Generating public/private rsa key pair. Enter file in which to save the key (/home/waldek/.ssh/id_rsa): my_ssh_key Enter passphrase (empty for no passphrase): Enter same passphrase again: Your identification has been saved in my_ssh_key. Your public key has been saved in my_ssh_key.pub. The key fingerprint is: SHA256:ndWgt3PjUjrdfaBMudQFJM8xCrjPKXlvg9TRYsWz2UQ waldek@helloworld The key's randomart image is: +---[RSA 2048]----+ | .. oo=.E| | . o B++.| | .. +o+*.| | .. ++++..| | S+o+*o* | | o *+.X +.| | + oB o +| | . +o .| | . . | +----[SHA256]-----+ ➜ ~ git:(master) ✗ ``` The current default is to generate an [RSA](https://en.wikipedia.org/wiki/RSA_(cryptosystem)) key of 2048 bits which is currently considered secure. You can change the scheme and bit depth with the `-t` and `-b` arguments respectively. Have a look at the `man ssh-keygen` pages for more info. ### Deploying keys Just generating a key is not that useful, we need to know how to **use** them. In order to understand that we need to have a look at how an ssh connection works. When you try to establish an ssh connection you can add a `-v` flag to make the output more verbose. You'll see output along the lines of this: ``` ➜ qualifying git:(master) ✗ ssh student@localhost -v OpenSSH_7.9p1 Debian-10+deb10u2, OpenSSL 1.1.1d 10 Sep 2019 debug1: Reading configuration data /home/waldek/.ssh/config debug1: Reading configuration data /etc/ssh/ssh_config debug1: /etc/ssh/ssh_config line 19: Applying options for * debug1: Connecting to localhost [127.0.0.1] port 22. debug1: Connection established. debug1: identity file /home/waldek/.ssh/id_rsa type 0 debug1: identity file /home/waldek/.ssh/id_rsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_dsa type -1 debug1: identity file /home/waldek/.ssh/id_dsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_ecdsa type -1 debug1: identity file /home/waldek/.ssh/id_ecdsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_ed25519 type -1 debug1: identity file /home/waldek/.ssh/id_ed25519-cert type -1 debug1: identity file /home/waldek/.ssh/id_xmss type -1 debug1: identity file /home/waldek/.ssh/id_xmss-cert type -1 debug1: Local version string SSH-2.0-OpenSSH_7.9p1 Debian-10+deb10u2 debug1: Remote protocol version 2.0, remote software version OpenSSH_7.9p1 Debian-10+deb10u2 debug1: match: OpenSSH_7.9p1 Debian-10+deb10u2 pat OpenSSH* compat 0x04000000 debug1: Authenticating to localhost:22 as 'student' debug1: SSH2_MSG_KEXINIT sent debug1: SSH2_MSG_KEXINIT received debug1: kex: algorithm: curve25519-sha256 debug1: kex: host key algorithm: ecdsa-sha2-nistp256 debug1: kex: server->client cipher: chacha20-poly1305@openssh.com MAC: compression: none debug1: kex: client->server cipher: chacha20-poly1305@openssh.com MAC: compression: none debug1: expecting SSH2_MSG_KEX_ECDH_REPLY debug1: Server host key: ecdsa-sha2-nistp256 SHA256:iALTEcfl6AjvOnT0TWBNrp/PsuWem/ZiP+uGRVEeFaE debug1: Host 'localhost' is known and matches the ECDSA host key. debug1: Found key in /home/waldek/.ssh/known_hosts:1 debug1: rekey after 134217728 blocks debug1: SSH2_MSG_NEWKEYS sent debug1: expecting SSH2_MSG_NEWKEYS debug1: SSH2_MSG_NEWKEYS received debug1: rekey after 134217728 blocks debug1: Will attempt key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k debug1: Will attempt key: /home/waldek/.ssh/id_dsa debug1: Will attempt key: /home/waldek/.ssh/id_ecdsa debug1: Will attempt key: /home/waldek/.ssh/id_ed25519 debug1: Will attempt key: /home/waldek/.ssh/id_xmss debug1: SSH2_MSG_EXT_INFO received debug1: kex_input_ext_info: server-sig-algs= debug1: SSH2_MSG_SERVICE_ACCEPT received debug1: Authentications that can continue: publickey,password debug1: Next authentication method: publickey debug1: Offering public key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k debug1: Authentications that can continue: publickey,password debug1: Trying private key: /home/waldek/.ssh/id_dsa debug1: Trying private key: /home/waldek/.ssh/id_ecdsa debug1: Trying private key: /home/waldek/.ssh/id_ed25519 debug1: Trying private key: /home/waldek/.ssh/id_xmss debug1: Next authentication method: password student@localhost's password: ``` The connection will try any form of authentication allowed by the server in order of most secure to least secure. Publickeys are considered more secure than passwords so it will try that first. You can see this at the following line `debug1: Will attempt key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k`. The `student` account does not have the matching public key as an authorized key so the client tries a password login next `debug1: Next authentication method: password`. On the server side the sshd process will look for a matching **public** key in the users home directory. By default it will try every line in the `~/.ssh/authorized_keys` file for authentication. If a match is found, you'll be granted access, if not it will try an other authentication method until every method allowed by the server is exhausted and you'll be denied access. The verbose output of a successful login with a key pair can be seen below. ``` ➜ ~ git:(master) ✗ ssh student@localhost -v OpenSSH_7.9p1 Debian-10+deb10u2, OpenSSL 1.1.1d 10 Sep 2019 debug1: Reading configuration data /home/waldek/.ssh/config debug1: Reading configuration data /etc/ssh/ssh_config debug1: /etc/ssh/ssh_config line 19: Applying options for * debug1: Connecting to localhost [127.0.0.1] port 22. debug1: Connection established. debug1: identity file /home/waldek/.ssh/id_rsa type 0 debug1: identity file /home/waldek/.ssh/id_rsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_dsa type -1 debug1: identity file /home/waldek/.ssh/id_dsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_ecdsa type -1 debug1: identity file /home/waldek/.ssh/id_ecdsa-cert type -1 debug1: identity file /home/waldek/.ssh/id_ed25519 type -1 debug1: identity file /home/waldek/.ssh/id_ed25519-cert type -1 debug1: identity file /home/waldek/.ssh/id_xmss type -1 debug1: identity file /home/waldek/.ssh/id_xmss-cert type -1 debug1: Local version string SSH-2.0-OpenSSH_7.9p1 Debian-10+deb10u2 debug1: Remote protocol version 2.0, remote software version OpenSSH_7.9p1 Debian-10+deb10u2 debug1: match: OpenSSH_7.9p1 Debian-10+deb10u2 pat OpenSSH* compat 0x04000000 debug1: Authenticating to localhost:22 as 'student' debug1: SSH2_MSG_KEXINIT sent debug1: SSH2_MSG_KEXINIT received debug1: kex: algorithm: curve25519-sha256 debug1: kex: host key algorithm: ecdsa-sha2-nistp256 debug1: kex: server->client cipher: chacha20-poly1305@openssh.com MAC: compression: none debug1: kex: client->server cipher: chacha20-poly1305@openssh.com MAC: compression: none debug1: expecting SSH2_MSG_KEX_ECDH_REPLY debug1: Server host key: ecdsa-sha2-nistp256 SHA256:iALTEcfl6AjvOnT0TWBNrp/PsuWem/ZiP+uGRVEeFaE debug1: Host 'localhost' is known and matches the ECDSA host key. debug1: Found key in /home/waldek/.ssh/known_hosts:1 debug1: rekey after 134217728 blocks debug1: SSH2_MSG_NEWKEYS sent debug1: expecting SSH2_MSG_NEWKEYS debug1: SSH2_MSG_NEWKEYS received debug1: rekey after 134217728 blocks debug1: Will attempt key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k debug1: Will attempt key: /home/waldek/.ssh/id_dsa debug1: Will attempt key: /home/waldek/.ssh/id_ecdsa debug1: Will attempt key: /home/waldek/.ssh/id_ed25519 debug1: Will attempt key: /home/waldek/.ssh/id_xmss debug1: SSH2_MSG_EXT_INFO received debug1: kex_input_ext_info: server-sig-algs= debug1: SSH2_MSG_SERVICE_ACCEPT received debug1: Authentications that can continue: publickey,password debug1: Next authentication method: publickey debug1: Offering public key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k debug1: Server accepts key: /home/waldek/.ssh/id_rsa RSA SHA256:tOuvE+Qq1B/eXyGcyIfs0MVXaaSI/GNYjLqO3D+Tz+k debug1: Authentication succeeded (publickey). Authenticated to localhost ([127.0.0.1]:22). debug1: channel 0: new [client-session] debug1: Requesting no-more-sessions@openssh.com debug1: Entering interactive session. debug1: pledge: network debug1: client_input_global_request: rtype hostkeys-00@openssh.com want_reply 0 debug1: Remote: /home/student/.ssh/authorized_keys:1: key options: agent-forwarding port-forwarding pty user-rc x11-forwarding debug1: Remote: /home/student/.ssh/authorized_keys:1: key options: agent-forwarding port-forwarding pty user-rc x11-forwarding debug1: Sending environment. debug1: Sending env LC_CTYPE = en_GB.UTF-8 debug1: Sending env LANG = en_GB.UTF-8 Linux helloworld 4.19.0-17-amd64 #1 SMP Debian 4.19.194-1 (2021-06-10) x86_64 The programs included with the Debian GNU/Linux system are free software; the exact distribution terms for each program are described in the individual files in /usr/share/doc/*/copyright. Debian GNU/Linux comes with ABSOLUTELY NO WARRANTY, to the extent permitted by applicable law. student@helloworld:~$ ``` ## Standard usage ## Tweaking the sshd configuration file All server configuration is done in the `/etc/ssh/sshd_config` file. Starting version TO_CHECK you can use the modern `/etc/ssh/sshd_config.d/` folder system to override default system configuration. This way any changes to the standard configuration made by the package maintainers won't mess with your custom preferences and tweaks. ### Version A modern sshd configuration will only allow version 2 but you can check or specify this in the configuration file. You'll probably never have to set this yourself but do keep it in mind when you're confronted with old installations. ``` Protocol Specifies the protocol versions sshd(8) supports. The possible values are ‘1’ and ‘2’. Multiple versions must be comma-separated. The default is ‘2’. Protocol 1 suffers from a number of cryptographic weaknesses and should not be used. It is only offered to support legacy devices. Note that the order of the protocol list does not indicate preference, because the client selects among multiple protocol versions offered by the server. Specifying “2,1” is identical to “1,2”. ``` ## Tunnels ## SFTP ## Autossh ## SSHFS ## SSHuttle